Another Rob Neyer book I've enjoyed is Rob Neyer's Big Book of Baseball Blunders. Like Baseball Legends, it is a bunch of bite-sized segments, and as the title suggests, it goes back and looks at some of the legendary mistakes -- particularly personnel-related -- in baseball history, and evaluates how big of an impact the blunder really had on the team in question.
You've got the decision to leave Bill Buckner in the game in the 9th inning, rather than subbing in Dave Stapleton, the decision by the Tigers to cut bait with a young minor leaguer named Carl Hubbell, and episodes like Bill Veeck's dealing spree with the ChiSox that resulted in an ungodly amount of young talent being dispersed in exchange for not much.
A fun read, with a lot of research, and some examination of what deals were reasonable enough moves that backfired horribly, and what deals just clearly didn't make sense at the time.
Another one of Neyer's books that I recommend checking out...